Ammonia → 2-Iodo-5-propoxy-benzamide

HRID 330836ノート

反応式

HRID 330836 の反応式
[OH-].[Na+].C[O:4][C:5](=O)[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:7]=1[I:16].Cl.C1N=C[N:21](C(N2C=NC=C2)=O)C=1.N>O.CO>[I:16][C:7]1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH3:15])=[CH:11][C:6]=1[C:5]([NH2:21])=[O:4]

参加物

8

反応物 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682631,1'-Carbonyldiimidazole2 回HCID 66611398HCID 66611398、化合物

生成物 1

HCID 666113302-Iodo-5-propoxy-benzamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

129 mL (258 mmol) 2N NaOH are added to 4.12 g (12.9 mmol) methyl-5-propoxy-2-iodobenzoate (XXVII.1) 60 mL MeOH. The mixture is stirred at 50° C. for 3 h. After that time, the mixture was acidified to pH 5 with 1N aq. HCl and extracted with EtOAc (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is taken up in 30 mL THF and 2.04 g (12.6 mmol) CDI are added. The mixture is stirred at rt for 1 h. Additional 0.5 eq CDI are added and stirring is continued for 20 min. 20 mL of 35% ammonia in water are added and the resulting mixture is stirred at rt for 5 min. The solvent was partly removed in vacuo until precipitation of a white solid. The product is filtered off and dried at 40° C. in vacuo.

後処理

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. stirringThe mixture is stirred at rt for 1 h
  6. stirringstirring
  7. waitis continued for 20 min
  8. stirringthe resulting mixture is stirred at rt for 5 min
  9. customThe solvent was partly removed in vacuo until precipitation of a white solid
  10. filtrationThe product is filtered off
  11. customdried at 40° C. in vacuo

出典と根拠

ORDレコード
ord-a8804ced20064a5292cf2fa3ed078121
出典データセット
uspto-grants-2014_11
特許番号
US08877754B2

反応ノート

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